IP Library Granted Patent US 7,560,167
Granted Patent B2
US 7,560,167 · App. 11/515,463 · Granted Jul 14, 2009

Composition containing anti-misting component

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Quick Facts
Patent No.
US 7,560,167
App. No.
11/515,463
Granted
Jul 14, 2009
Kind
B2
Abstract

The invention relates to coating formulations comprising (i) a silicone-based coating component susceptible to misting under mist-producing conditions; and (ii) an anti-misting amount of a branched polysiloxane component resulting from copolymerizing under hydrosilylation conditions a component mixture comprising (a) one or more organosilicon compounds containing at least two unsaturated hydrocarbon functional groups per molecule, and (b) one or more silylhydride-containing compounds containing at least two silylhydride functional groups per molecule, with the provision that (i) at least one component (a) or (b) contains at least three functional groups per molecule; (ii) a component (a) or (b) having a higher number of functional groups per molecule is present in a molar amount equal to or lower than a molar amount of the other component (a) or (b) having a lower number of functional groups per molecule; and (iii) unsaturated hydrocarbon compounds are excluded from the component mixture. The invention also relates to a process for coating a substrate with the above coating formulation, as well as hardened silicone-based coatings or films obtained by subjecting the coated substrate to one or more curing steps.

Claims (64)

1. A composition comprising:

(i) a silicone-based coating component susceptible to misting under mist-producing conditions; and

(ii) an anti-misting amount of a branched polysiloxane component resulting from copolymerizing under hydrosilylation conditions a component mixture comprising:

(a) one or more organosilicon compounds containing at least two unsaturated hydrocarbon functional groups per molecule, said unsaturated hydrocarbon functional groups capable of undergoing a hydrosilylation reaction with a silylhydride-containing compound under hydrosilylation conditions, provided that when said component (a) is a polysiloxane it contains at least one D or T silicone unit that contains at least one unsaturated hydrocarbon functional group; and

(b) one or more silylhydride-containing compounds containing at least two silylhydride functional groups per molecule;

provided that (i) at least one component (a) or (b) contains at least three functional groups per molecule; (ii) when one component (a) or (b) has a higher number of functional groups per molecule than another component (a) or (b) having a lower number of functional groups per molecule, then the component (a) or (b) having a higher number of functional groups per molecule is present in a molar amount equal to or lower than the molar amount of the component (a) or (b) having a lower number of functional groups per molecule; and (iii) unsaturated hydrocarbon compounds are excluded from the component mixture.

2. The composition of claim 1 , wherein the unsaturated hydrocarbon functional groups of component (a) are in a molar ratio to silylhydride functional groups of component (b) within a range according to a formula (6−s):1 or 1:(1+t) where s represents a number equal to or greater than 0 and less than 5, and t represents a number greater than 0 and equal to or less than 5.

3. The composition of claim 1 , wherein the unsaturated hydrocarbon functional groups of component (a) are in a molar ratio to silylhydride functional groups of component (b) within a range according to a formula (4.6−s):1 or 1:(1+s) where s represents a number greater than 0 and less than 3.6.

4. The composition of claim 1 , wherein the unsaturated hydrocarbon functional groups of component (a) are in a molar ratio to silylhydride functional groups of component (b) within a range according to a formula (4.25−s):1 or 1:(1+t) where s represents a number equal to or greater than 0 and less than 3.25, and t represents a number greater than 0 and equal to or less than 3.25.

5. The composition of claim 1 , wherein the unsaturated hydrocarbon functional groups of component (a) are in a molar ratio to silylhydride functional groups of component (b) within a range according to a formula (4.6−s):1 where s represents a number greater than 0 and less than 3.6.

6. The composition of claim 1 , wherein the unsaturated hydrocarbon functional groups of component (a) are in a molar ratio to silylhydride functional groups of component (b) within a range of about 4.5:1 to about 2:1.

7. The composition of claim 1 , wherein one component (a) or (b) has at least four functional groups per molecule and is in a lower molar amount than the other component (a) or (b) having two or three functional groups per molecule.

8. The composition of claim 1 , wherein one component (a) or (b) has at least six functional groups per molecule and is in a lower molar amount than the other component (a) or (b) having two or three functional groups per molecule.

9. A composition comprising:

(i) a silicone-based coating component susceptible to misting under mist-producing conditions; and

(ii) an anti-misting amount of a branched polysiloxane component resulting from copolymerizing under hydrosilylation conditions a component mixture comprising:

(a) one or more organosilicon compounds containing at least two unsaturated hydrocarbon functional groups per molecule, said unsaturated hydrocarbon functional groups capable of undergoing a hydrosilylation reaction with a silylhydride-containing compound under hydrosilylation conditions, provided that when said component (a) is a polysiloxane it contains at least one D or T silicone unit that contains at least one unsaturated hydrocarbon functional group; and

(b) one or more silylhydride-containing compounds containing at least two silylhydride functional groups per molecule;

provided that (i) at least one component (a) or (b) contains at least three functional groups per molecule; (ii) one component (a) or (b) has a higher number of functional groups per molecule and is in a lower molar amount than another component (a) or (b) having a lower number of functional groups per molecule; and (iii) unsaturated hydrocarbon compounds are excluded from the component mixture.

10. A composition comprising:

(i) a silicone-based coating component susceptible to misting under mist-producing conditions; and

(ii) an anti-misting amount of a branched polysiloxane component resulting from copolymerizing under hydrosilylation conditions a component mixture comprising:

(a) one or more organosilicon compounds containing at least two unsaturated hydrocarbon functional groups per molecule, said unsaturated hydrocarbon functional groups capable of undergoing a hydrosilylation reaction with a silylhydride-containing compound under hydrosilylation conditions, provided that when said component (a) is a polysiloxane it contains at least one D or T silicone unit that contains at least one unsaturated hydrocarbon functional group; and

(b) one or more silylhydride-containing compounds containing at least two silylhydride functional groups per molecule;

provided that (i) at least one component (a) or (b) contains at least three functional groups per molecule; (ii) unsaturated hydrocarbon functional groups of component (a) are in a molar ratio to silylhydride functional groups of component (b) within a range of about (6−s):1 or about 1:(1+t) where s represents a number equal to or greater than 0 and less than 5, and t represents a number greater than 0 and equal to or less than 5; (iii) one component (a) or (b) has a higher number of functional groups per molecule and is in a lower molar amount than another component (a) or (b) having a lower number of functional groups per molecule; (iv) unsaturated hydrocarbon compounds are excluded from the component mixture.

11. A composition comprising:

(i) a silicone-based coating component susceptible to misting under mist-producing conditions; and

(ii) an anti-misting amount of a branched polysiloxane component resulting from copolymerizing under hydrosilylation conditions a component mixture comprising:

(a) one or more organosilicon compounds containing at least two unsaturated hydrocarbon functional groups per molecule, said unsaturated hydrocarbon functional groups capable of undergoing a hydrosilylation reaction with a silylhydride-containing compound under hydrosilylation conditions, provided that when said component (a) is a polysiloxane it contains at least one D or T silicone unit that contains at least one unsaturated hydrocarbon functional group; and

(b) one or more silylhydride-containing compounds containing at least two silylhydride functional groups per molecule;

provided that (i) at least one component (a) or (b) contains at least three functional groups per molecule; (ii) unsaturated hydrocarbon functional groups of component (a) are in a molar ratio to silylhydride functional groups of component (b) within a range according to a formula (4.6−s):1 or 1:(1+s) where s represents a number greater than 0 and less than 3.6; (iii) one component (a) or (b) has a higher number of functional groups per molecule and is in a lower molar amount than another component (a) or (b) having a lower number of functional groups per molecule; (iv) unsaturated hydrocarbon compounds are excluded from the component mixture.

12. A composition comprising:

(i) a silicone-based coating component susceptible to misting under mist-producing conditions; and

(ii) an anti-misting amount of a branched polysiloxane component resulting from copolymerizing under hydrosilylation conditions a component mixture comprising:

(a) one or more organosilicon compounds containing unsaturated hydrocarbon functional groups, said unsaturated hydrocarbon functional groups capable of undergoing a hydrosilylation reaction with a silylhydride-containing compound under hydrosilylation conditions, provided that when said component (a) is a polysiloxane it contains at least one D or T silicone unit that contains at least one unsaturated hydrocarbon functional group; and

(b) one or more silylhydride-containing compounds containing silylhydride functional groups;

provided that (i) one component (a) or (b) has at least four functional groups per molecule and is in a lower molar amount than another component (a) or (b) having two or three functional groups per molecule; (ii) unsaturated hydrocarbon functional groups of component (a) are in a molar ratio to silylhydride functional groups of component (b) within a range of about (6−s):1 or about 1:(1+t) where s represents a number equal to or greater than 0 and less than 5, and t represents a number greater than 0 and equal to or less than 5; and (iii) unsaturated hydrocarbon compounds are excluded from the component mixture.

13. A composition comprising:

(i) a silicone-based coating component susceptible to misting under mist-producing conditions; and

(ii) an anti-misting amount of a branched polysiloxane component resulting from copolymerizing under hydrosilylation conditions a component mixture comprising:

(a) one or more organosilicon compounds containing unsaturated hydrocarbon functional groups, said unsaturated hydrocarbon functional groups capable of undergoing a hydrosilylation reaction with a silylhydride-containing compound under hydrosilylation conditions, provided that when said component (a) is a polysiloxane it contains at least one D or T silicone unit that contains at least one unsaturated hydrocarbon functional group; and

(b) one or more silylhydride-containing compounds containing silylhydride functional groups;

provided that (i) one component (a) or (b) has at least six functional groups per molecule and is in a lower molar amount than another component (a) or (b) having two or three functional groups per molecule; (ii) unsaturated hydrocarbon functional groups of component (a) are in a molar ratio to silylhydride functional groups of component (b) within a range of about (6−s):1 or about 1:(1+t) where s represents a number equal to or greater than 0 and less than 5, and t represents a number greater than 0 and equal to or less than 5; and (iii) unsaturated hydrocarbon compounds are excluded from the component mixture.

14. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 1 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

15. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 2 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

16. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 3 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

17. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 4 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

18. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 5 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

19. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 6 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

20. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 7 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

21. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 8 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

22. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 9 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

23. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 10 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

24. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 11 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

25. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 12 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

26. A coating process comprising applying to a substrate under mist-producing conditions the composition of claim 13 , the composition exhibiting reduced misting when subjected to said mist-producing conditions as compared to the same composition lacking an anti-misting amount of branched polysiloxane component.

27. A hardened silicone-based coating or film produced by subjecting a substrate coated with the composition of claim 1 to one or more curing steps.

28. A hardened silicone-based coating or film produced by subjecting a substrate coated with the composition of claim 10 to one or more curing steps.

29. A composition comprising:

(i) a silicone-based coating component susceptible to misting under mist-producing conditions; and

(ii) an anti-misting amount of a branched polysiloxane component resulting from copolymerizing under hydrosilylation conditions a component mixture comprising:

(a) one or more organosilicon compounds containing at least two unsaturated hydrocarbon functional groups per molecule, said unsaturated hydrocarbon functional groups capable of undergoing a hydrosilylation reaction with a silylhydride-containing compound under hydrosilylation conditions, provided that when component (a) is a polysiloxane it contains at least three unsaturated hydrocarbon functional groups per molecule; and

(b) one or more silylhydride-containing compounds containing at least two silylhydride functional groups per molecule;

provided that (i) at least one component (a) or (b) contains at least three functional groups per molecule; (ii) when one component (a) or (b) has a higher number of functional groups per molecule than another component (a) or (b) having a lower number of functional groups per molecule, then the component (a) or (b) having a higher number of functional groups per molecule is present in a molar amount equal to or lower than the molar amount of the component (a) or (b) having a lower number of functional groups per molecule; and (iii) unsaturated hydrocarbon compounds are excluded from the component mixture.

Assignments (22)
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (063213/0472) Recorded Oct 22, 2025
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 073168/0715 →
RELEASE OF SECURITY INTEREST Recorded Jul 18, 2025
From: KOOKMIN BANK NEW YORK BRANCH
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 072039/0906 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded Mar 31, 2023
From: BNP PARIBAS
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063259/0133 →
FIRST LIEN TERM LOAN PATENT SECURITY AGREEMENT Recorded Mar 31, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 063213/0472 →
RELEASE OF SECURITY INTEREST Recorded Mar 30, 2023
From: KOOKMIN BANK NEW YORK
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 063197/0373 →
SECURITY INTEREST Recorded Mar 30, 2023
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK NEW YORK BRANCH
Reel/Frame 063197/0475 →
RELEASE OF SECURITY INTEREST Recorded Dec 24, 2020
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 054883/0855 →
FIRST LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BNP PARIBAS, AS ADMINISTRATIVE AGENT
Reel/Frame 049387/0782 →
ABL PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.; MOMENTIVE PERFORMANCE MATERIALS GMBH
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0252 →
SECOND LIEN TERM LOAN PATENT AGREEMENT Recorded Jun 5, 2019
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: KOOKMIN BANK, NEW YORK BRANCH, AS ADMINISTRATIVE AGENT
Reel/Frame 049388/0220 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENTS Recorded May 21, 2019
From: JPMORGAN CHASE BANK, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 050304/0555 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049249/0271 →
RELEASE OF SECURITY INTEREST Recorded May 15, 2019
From: BOKF, NA
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 049194/0085 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY - SECOND LIEN Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035137/0263 →
NOTICE OF CHANGE OF COLLATERAL AGENT - ASSIGNMENT OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Mar 6, 2015
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A. AS COLLATERAL AGENT
To: BOKF, NA, AS SUCCESSOR COLLATERAL AGENT
Reel/Frame 035136/0457 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0252 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT RIGHTS Recorded Oct 30, 2014
From: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A.
To: MOMENTIVE PERFORMANCE MATERIALS INC.
Reel/Frame 034113/0331 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0570 →
SECURITY INTEREST Recorded Oct 27, 2014
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: THE BANK OF NEW YORK MELLON TRUST COMPANY, N.A., AS COLLATERAL AGENT
Reel/Frame 034066/0662 →
SECURITY AGREEMENT Recorded Apr 29, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 030311/0343 →
PATENT SECURITY AGREEMENT Recorded Apr 3, 2013
From: MOMENTIVE PERFORMANCE MATERIALS INC.
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 030185/0001 →
SECURITY AGREEMENT Recorded May 31, 2012
From: MOMENTIVE PERFORMANCE MATERIALS INC
To: BANK OF NEW YORK MELLON TRUST COMPANY, N.A., THE
Reel/Frame 028344/0208 →